Synthesis of some proline derivatives by means of michael additions of glycine esters

✍ Scribed by Anne van der Werf; Richard M. Kellogg

• Book ID: 104216182
• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 207 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79779-6

✦ Synopsis

Addition of the Schiff bases derived from reaction of glycine alkyl esters with benzophenoneimine to a,R-unsaturated ketones, followed by hydrogenation of the addition products, leads to 5-or 3,5-substituted prolines. Hydrolysis of the Michael adducts rather than hydrogenation allows synthesis of '-pyrrolines as stable, isolable intermediates. Alkylated amino acids in general,' and alkyl substituted prolines' in 'gHS 0 + CbH5 L CO>Alk CO,Alk R, 2 R, 1 _ a) R1-CHg, R,-H b) R,+H, R,=H Alk-CH,, C,H, c) R,=CH3,'R,-CH, d *2 / fi d 4 COzAlk R, N H CO,Alk 5a-c &a-b a)10 mol% cszco,; b) 1N HC1/(C2H,),0;